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The precursor ensemble to the orchestra was the Milwaukee Pops Orchestra, a part-time ensemble which had been founded 10 years earlier. In 1959, the orchestra formally changed its name to the Milwaukee Symphony Orchestra, with Harry John Brown as its first music director. During his nine-year tenure, Brown led the orchestra's transition from a semi-professional pops group to a fully professional, full-time symphony orchestra.

During the tenure of Kenneth Schermerhorn, the orchestra's second music director, from 1968 to 1980, the orchestra had begun its 'State Tour' programme of concerts around Wisconsin, to such cities as Fish Creek, Fond du Lac, Marinette, Ripon, Rhinelander, Three Lakes, West Bend, and Whitewater, Wisconsin, as well as Naperville, Illinois. The orchestra also initiated its concerts for students, as well as giving its first performance at Carnegie Hall. The Milwaukee Symphony Chorus was also established during this time. Lukas Foss served as the orchestra's third music director, from 1981 to 1986, which saw a notable increase in performances of contemporary music and American compositions, along with the orchestra's first European tour in 1986.

Zdenek Macal was the orchestra's fourth music director, from 1986 to 1995. The orchestra began to record for Koss Classics during this period, and established its Arts in Community Education programme in 1990. From 1995 to 1997, Stanisław Skrowaczewski served as the orchestra's artistic advisor, prior to the advent of Andreas Delfs as the orchestra's fifth music director. Delfs was music director from 1997 to 2009. During his tenure, in 1999, the orchestra performed in Cuba, the first American symphony orchestra to do so since the U.S. embargo against Cuba was implemented in 1962. Delfs became the orchestra's conductor laureate after the conclusion of his tenure in 2009.

The orchestra's current music director is Edo de Waart, since 2009, having been named to the post in January 2008.[1] In February 2015, the orchestra announced the scheduled conclusion of de Waart's tenure as music director at the end of the 2016-2017 season, after which he is scheduled to become the orchestra's conductor laureate.[2]

The orchestra's resident conductor is Francesco Lecce-Chong, since 2011. Past principal Pops conductors have included Doc Severinsen, who currently holds the title of principal Pops conductor emeritus, and Marvin Hamlisch.